US20080114029A1 - Polymorphs of solifenacin intermediate - Google Patents
Polymorphs of solifenacin intermediate Download PDFInfo
- Publication number
- US20080114029A1 US20080114029A1 US11/890,264 US89026407A US2008114029A1 US 20080114029 A1 US20080114029 A1 US 20080114029A1 US 89026407 A US89026407 A US 89026407A US 2008114029 A1 US2008114029 A1 US 2008114029A1
- Authority
- US
- United States
- Prior art keywords
- solifenacin
- phenyl
- tetrahydroisoquinoline
- crystalline form
- iql
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- FBOUYBDGKBSUES-VXKWHMMOSA-N solifenacin Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-VXKWHMMOSA-N 0.000 title claims abstract description 25
- 229960003855 solifenacin Drugs 0.000 title claims description 12
- PRTRSEDVLBBFJZ-HNNXBMFYSA-N (1s)-1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1([C@H]2C3=CC=CC=C3CCN2)=CC=CC=C1 PRTRSEDVLBBFJZ-HNNXBMFYSA-N 0.000 claims abstract description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 25
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 18
- 229940095064 tartrate Drugs 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000001144 powder X-ray diffraction data Methods 0.000 claims description 12
- FBOUYBDGKBSUES-KEKNWZKVSA-N 1-azabicyclo[2.2.2]octan-3-yl (1s)-1-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C1([C@H]2C3=CC=CC=C3CCN2C(OC2C3CCN(CC3)C2)=O)=CC=CC=C1 FBOUYBDGKBSUES-KEKNWZKVSA-N 0.000 claims description 11
- 229960001368 solifenacin succinate Drugs 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 description 13
- 238000000634 powder X-ray diffraction Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- -1 ester succinate Chemical class 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- IVLICPVPXWEGCA-ZETCQYMHSA-N (3r)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC2[C@@H](O)CN1CC2 IVLICPVPXWEGCA-ZETCQYMHSA-N 0.000 description 1
- PRTRSEDVLBBFJZ-UHFFFAOYSA-N 1-phenyl-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC=CC=C2C1C1=CC=CC=C1 PRTRSEDVLBBFJZ-UHFFFAOYSA-N 0.000 description 1
- YSPDISPRPJFBCV-UHFFFAOYSA-N C1=CC=C(C2CCCC3=CC=CC=C32)C=C1 Chemical compound C1=CC=C(C2CCCC3=CC=CC=C32)C=C1 YSPDISPRPJFBCV-UHFFFAOYSA-N 0.000 description 1
- 206010020853 Hypertonic bladder Diseases 0.000 description 1
- 206010027566 Micturition urgency Diseases 0.000 description 1
- RXZMMZZRUPYENV-VROPFNGYSA-N O=C(O)CCC(=O)O.O=C(O[C@H]1CN2CCC1CC2)N1CCC2=CC=CC=C2[C@@H]1C1=CC=CC=C1 Chemical compound O=C(O)CCC(=O)O.O=C(O[C@H]1CN2CCC1CC2)N1CCC2=CC=CC=C2[C@@H]1C1=CC=CC=C1 RXZMMZZRUPYENV-VROPFNGYSA-N 0.000 description 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 description 1
- 206010036018 Pollakiuria Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000020629 overactive bladder Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940063390 vesicare Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
Definitions
- the present invention is related to solid state chemistry of 1-phenyl-1,2,3,4-tetrahydroisoquinoline, which is a useful intermediate for making solifenacin succinate.
- IQL 1-Pheny-1,2,3,4-tetrahydroisoquinoline
- Solifenacin succinate (3R)-1-azabicyclo[2.2.2]oct-3-yl-(1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate-succinate, or 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester succinate of the formula
- the drug is a urinary antispasmodic indicated for the treatment of urge incontinence and/or increased urinary frequency and urgency as may occur in patients with overactive bladder syndrome (“OAB”).
- OAB overactive bladder syndrome
- the drug is marketed under the name Vesicare® in 5 mg and 10 mg tablets.
- Solifenacin and derivatives thereof, as well as salts thereof, are reported to encompass in U.S. Pat. No. 6,017,927.
- Polymorphism the occurrence of different solid state forms, is a property of some molecules and molecular complexes.
- a single molecule like solifenacin base, may give rise to a variety of solid state forms having distinct crystal structures and physical properties such as melting point, powder x-ray diffraction (“PXRD”) pattern, infrared (“IR”) absorption fingerprint, and solid state nuclear magnetic resonance (“NMR”) spectrum.
- PXRD powder x-ray diffraction
- IR infrared
- NMR solid state nuclear magnetic resonance
- One solid state form may give rise to thermal behavior different from that of another solid state form. Thermal behavior can be measured in the laboratory by such techniques as capillary melting point, thermogravimetric analysis (“TGA”), and differential scanning calorimetry (“DSC”), which have been used to distinguish polymorphic forms.
- TGA thermogravimetric analysis
- DSC differential scanning calorimetry
- polymorphs are distinct solids sharing the same molecular formula yet having distinct advantageous physical properties compared to other solid state forms of the same compound or complex.
- One of the most important physical properties of pharmaceutical compounds is their solubility in aqueous solution, particularly their solubility in the gastric juices of a patient.
- solubility in aqueous solution, particularly their solubility in the gastric juices of a patient.
- a drug that is unstable to conditions in the patient's stomach or intestine it is often desirable for a drug that is unstable to conditions in the patient's stomach or intestine to dissolve slowly so that it does not accumulate in a deleterious environment.
- Different solid state forms or polymorphs of the same pharmaceutical compounds can and reportedly do have different aqueous solubilities.
- the invention encompasses a crystalline form of 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline (“(S)-IQL”), of the following formula
- the invention encompasses a crystalline form of (S)-IQL characterized by PXRD peaks at about 10.2, 12.4, 15.4, and 16.3° ⁇ 0.2° 2 ⁇ containing not more than about 10 wt %, preferably not more than about 5 wt %, and more preferably not more than about 1 wt % of other crystalline form of (S)-IQL.
- the invention encompasses a process for preparing a crystalline form of (S)-IQL characterized by PXRD pattern with peaks at about 10.2, 12.4, 15.4, and 16.3 ⁇ 0.2 °2 ⁇ , comprising combining (S)-IQL tartrate with water, an inorganic base, and an organic solvent.
- the invention encompasses a process for preparing a crystalline form of (S)-IQL characterized by PXRD pattern with peaks at about 10.2, 12.4, 15.4, and 16.3 ⁇ 0.2 °2 ⁇ , comprising slurrying (S)-IQL tartrate in water and adding an inorganic base.
- the invention encompasses a process for preparing a solifenacin salt by preparing according to the processes described above and converting it to a pharmaceutically acceptable salt of solifenacin.
- FIG. 1 illustrates PXRD pattern of S-IQL characterized by peaks at about 10.2, 12.4, 15.4, and 16.3 ⁇ 0.2°2 ⁇ .
- room temperature or “RT” refers to the ambient temperature of a typical laboratory, which is usually about 15° C. to about 30° C., often about 18° C. to about 25° C.
- vacuum refers to a pressure of about to 2 mmHg to about 100 mmHg.
- polymorphic purity refers to the purity of one polymorphic form with respect to other polymorphic forms
- enantiomeric purity refers to the purity of an enantiomer with respect to the other enantiomer.
- IQL refers to 1-pheny-1,2,3,4-tetrahydroisoquinoline
- (S)-IQL refers to 1(S)-phenyl-1,2,3,4-tetraisoquinoline
- (S)-IQL tartrate refers to 1(S)-phenyl-1,2,3,4-tetraisoquinoline tartrate.
- PXRD powder X-ray diffraction
- the invention encompasses a crystalline form of 1(S)-phenyl-1,2,3,4-tetrahydroisoquinoline, of the following formula
- the crystalline form of (S)-IQL may be further characterized by data selected from a group consisting of PXRD pattern with peaks at about 18.9, 20.1, 22.1, 22.8, 24.6, and 17.4 ⁇ 0.2 °2 ⁇ and PXRD pattern substantially as depicted in FIG. 1 .
- the above crystalline form of (S)-IQL characterized by PXRD peaks at about 10.2, 12.4, 15.4, and 16.3° ⁇ 0.2° 2 ⁇ containing not more than about 10 wt %, preferably not more than about 5 wt %, and more preferably not more than about 1 wt % of other crystalline form of (S)-IQL.
- the polymorphic purity is measured by PXRD.
- the invention encompasses a process for preparing a crystalline form of (S)-IQL characterized by PXRD pattern with peaks at about 10.2, 12.4, 15.4, and 16.3 ⁇ 0.2 °2 ⁇ , comprising combining (S)-IQL tartrate with water, an inorganic base, and an organic solvent.
- the (S)-IQL tartrate may be obtained according to U.S. Patent Application No. 60/949,112.
- the inorganic base is selected from the group consisting of NaOH, KOH, NaHCO 3 , KHCO 3 , Na2CO 3 , K 2 CO 3 , and mixtures thereof. More preferably, the base is NaOH.
- the organic solvent is selected from the group consisting of toluene, THF, and mixtures thereof.
- the combining step is at about room temperature.
- a two phase system is obtained.
- the two phases are separated.
- the crystalline form is obtained from the organic phase.
- the crystalline form is obtained by evaporating the organic phase.
- the invention encompasses a process for preparing a crystalline form of (S)-IQL characterized by PXRD pattern with peaks at about 10.2, 12.4, 15.4, and 16.3 ⁇ 0.2 °2 ⁇ , comprising slurrying (S)-IQL tartrate in water and adding an inorganic base.
- the base is selected from the group consisting of NaOH, KOH, NaHCO 3 , KHCO 3 , Na2CO 3 , K 2 CO 3 , and mixtures thereof. More preferably, the base is NaOH.
- the base is added gradually to the slurry.
- the base is added to obtain a pH of about 10 to about 14, more preferably of about 12.
- the process further comprises recovering the crystalline form.
- the recovery comprises isolating, washing, and drying.
- the isolation is by filtration.
- the washing is with water.
- the drying is at about 40° C. to about 60° C., more preferably at about 55° C.
- the drying is under vacuum.
- the drying is over night.
- the invention encompasses a process for preparing a solifenacin salt by preparing (S)-IQL according to the processes described above and converting it to a pharmaceutically acceptable salt of solifenacin.
- the solifenacin salt is selected from the group consisting of solifenacin succinate, solifenacin acetate, and solifenacin-HX, wherein X is a halogen atom, preferably Cl. More preferably, the solifenacin salt is solifenacin succinate.
- (S)-IQL may be converted to (S)-IQL alkyl carbamate by reacting with an alkyl carbamate, for example, according to the methods disclosed in U.S. patent application Ser. No. 11/645,021, which is incorporated herein by reference.
- (S)-IQL alkyl carbamate may be converted to solifenacin by reacting with 3(R)-quinuclidinol in the presence of base, for example, according to the methods disclosed in U.S. Patent Application No. 60/930,391 and U.S. patent application Ser. No. 11/645,021.
- Solifenacin may be converted to solifenacin succinate by reacting with succinic acid, for example, according to the methods disclosed in U.S. Patent Application No. 60/930,391 and U.S. patent application Ser. No. 11/645,021.
- X-Ray Powder Diffractions were performed on ARL (Scintag) X-Ray powder diffractometer model X'TRA, Cu-tube, solid state detector. A round standard aluminum sample holder with round zero background quartz plate was used. Scanning parameters: range 2-40° 2 ⁇ , continuous scan, rate 5 deg/min.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/890,264 US20080114029A1 (en) | 2006-08-03 | 2007-08-03 | Polymorphs of solifenacin intermediate |
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83580606P | 2006-08-03 | 2006-08-03 | |
| US84526006P | 2006-09-18 | 2006-09-18 | |
| US84526106P | 2006-09-18 | 2006-09-18 | |
| US85995106P | 2006-11-20 | 2006-11-20 | |
| US85995206P | 2006-11-20 | 2006-11-20 | |
| US87891307P | 2007-01-04 | 2007-01-04 | |
| US89878907P | 2007-01-31 | 2007-01-31 | |
| US89888807P | 2007-01-31 | 2007-01-31 | |
| US93039107P | 2007-05-15 | 2007-05-15 | |
| US94911207P | 2007-07-11 | 2007-07-11 | |
| US11/890,264 US20080114029A1 (en) | 2006-08-03 | 2007-08-03 | Polymorphs of solifenacin intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20080114029A1 true US20080114029A1 (en) | 2008-05-15 |
Family
ID=39033485
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/890,264 Abandoned US20080114029A1 (en) | 2006-08-03 | 2007-08-03 | Polymorphs of solifenacin intermediate |
| US11/890,289 Abandoned US20080091023A1 (en) | 2006-08-03 | 2007-08-03 | Processes for optical resolution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline |
| US11/890,316 Abandoned US20080114171A1 (en) | 2006-08-03 | 2007-08-03 | Solifenacin base forms and preparation thereof |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/890,289 Abandoned US20080091023A1 (en) | 2006-08-03 | 2007-08-03 | Processes for optical resolution of 1-phenyl-1,2,3,4-tetrahydroisoquinoline |
| US11/890,316 Abandoned US20080114171A1 (en) | 2006-08-03 | 2007-08-03 | Solifenacin base forms and preparation thereof |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US20080114029A1 (fr) |
| EP (3) | EP1945636A2 (fr) |
| IL (1) | IL196271A0 (fr) |
| WO (3) | WO2008019057A2 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100298371A1 (en) * | 2007-12-04 | 2010-11-25 | Mayank Ghanshyambhai Dave | Process for preparing chemically and chirally pure solifenacin base and its salts |
| WO2011048607A1 (fr) | 2009-09-25 | 2011-04-28 | Cadila Healthcare Limited | Procédés de préparation de solifénacine ou d'un de ses sels |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009538362A (ja) * | 2007-07-13 | 2009-11-05 | テバ ファーマシューティカル インダストリーズ リミティド | ソリフェナシンの調製方法 |
| PL385265A1 (pl) | 2008-05-23 | 2009-12-07 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Sposób wytwarzania solifenacyny i/lub jej soli o wysokiej czystości farmaceutycznej |
| PL385264A1 (pl) * | 2008-05-23 | 2009-12-07 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Sposób wytwarzania enancjomerycznie czystej (S)-1-fenylo-1, 2, 3, 4-tetrahydroizochinoliny |
| SI3067353T1 (en) | 2008-07-29 | 2018-03-30 | Krka, D.D., Novo Mesto | Process for the preparation of solifenacin salts and their inclusion in pharmaceutical dosage forms |
| JP2012036093A (ja) * | 2008-12-15 | 2012-02-23 | Kaneka Corp | （ｓ）−１−フェニル−１，２，３，４−テトラヒドロイソキノリンの製造法 |
| CN103787969B (zh) | 2012-10-30 | 2016-07-06 | 上海京新生物医药有限公司 | 一种(1s)-1-苯基-3,4-二氢-2（1h）-异喹啉甲酸酯的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4923983A (en) * | 1989-07-31 | 1990-05-08 | Eli Lilly And Company | Method of resolving cis 3-amino-4-[2-(2-furyl)eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one |
| NO2005012I1 (no) * | 1994-12-28 | 2005-06-06 | Debio Rech Pharma Sa | Triptorelin og farmasoytisk akseptable salter derav |
| GB9606474D0 (en) * | 1996-03-27 | 1996-06-05 | Orion Yhytmo Oy | Method for obtaining pure enantiomers of a pyridazinone derivative |
| JP2001288171A (ja) * | 2000-04-10 | 2001-10-16 | Sumitomo Chem Co Ltd | 光学活性テトラヒドロイソキノリン誘導体の製造方法 |
| JPWO2005075474A1 (ja) * | 2004-02-09 | 2007-10-11 | アステラス製薬株式会社 | コハク酸ソリフェナシン含有組成物 |
| WO2005077364A1 (fr) * | 2004-02-18 | 2005-08-25 | Yamanouchi Pharmaceutical Co., Ltd. | Préparation transdermique de solifénacine et procédé d'amélioration de la perméabilité transdermique de celle-ci |
| CA2560080A1 (fr) * | 2004-03-16 | 2005-09-22 | Astellas Pharma Inc. | Composition contenant de la solifenacine |
| JPWO2005087231A1 (ja) * | 2004-03-16 | 2008-01-24 | アステラス製薬株式会社 | ソリフェナシン含有組成物 |
| PT2156824E (pt) * | 2004-03-25 | 2013-01-04 | Astellas Pharma Inc | Uma composição de solifenacina, ou um seu sal, utilizada sob a forma de formulações sólidas |
| US20090326230A1 (en) * | 2006-07-19 | 2009-12-31 | Dr. Reddy's Laboratories Ltd. | Process for preparing solifenacin and its salts |
-
2007
- 2007-08-03 US US11/890,264 patent/US20080114029A1/en not_active Abandoned
- 2007-08-03 WO PCT/US2007/017330 patent/WO2008019057A2/fr not_active Ceased
- 2007-08-03 US US11/890,289 patent/US20080091023A1/en not_active Abandoned
- 2007-08-03 US US11/890,316 patent/US20080114171A1/en not_active Abandoned
- 2007-08-03 EP EP07836479A patent/EP1945636A2/fr not_active Withdrawn
- 2007-08-03 EP EP07836504A patent/EP1943248A2/fr not_active Withdrawn
- 2007-08-03 WO PCT/US2007/017327 patent/WO2008019055A2/fr not_active Ceased
- 2007-08-03 WO PCT/US2007/017402 patent/WO2008019103A2/fr not_active Ceased
- 2007-08-03 EP EP07836477A patent/EP1922308A2/fr not_active Withdrawn
-
2008
- 2008-12-30 IL IL196271A patent/IL196271A0/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100298371A1 (en) * | 2007-12-04 | 2010-11-25 | Mayank Ghanshyambhai Dave | Process for preparing chemically and chirally pure solifenacin base and its salts |
| EP2484681A1 (fr) | 2007-12-04 | 2012-08-08 | Cadila Healthcare Limited | Sel de gentisate pur chimiquement et chiralement de solifénacine |
| EP2489666A2 (fr) | 2007-12-04 | 2012-08-22 | Cadila Healthcare Limited | Base de solifénacine pure chimiquement et chiralement et ses sels |
| WO2011048607A1 (fr) | 2009-09-25 | 2011-04-28 | Cadila Healthcare Limited | Procédés de préparation de solifénacine ou d'un de ses sels |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080114171A1 (en) | 2008-05-15 |
| WO2008019055A3 (fr) | 2008-08-21 |
| WO2008019103A2 (fr) | 2008-02-14 |
| WO2008019057A2 (fr) | 2008-02-14 |
| WO2008019055A2 (fr) | 2008-02-14 |
| US20080091023A1 (en) | 2008-04-17 |
| EP1945636A2 (fr) | 2008-07-23 |
| EP1922308A2 (fr) | 2008-05-21 |
| WO2008019103A3 (fr) | 2008-07-31 |
| IL196271A0 (en) | 2009-11-18 |
| WO2008019057A3 (fr) | 2008-07-10 |
| EP1943248A2 (fr) | 2008-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20080114029A1 (en) | Polymorphs of solifenacin intermediate | |
| US8217061B2 (en) | Polymorphs of sorafenib tosylate and sorafenib hemi-tosylate, and processes for preparation thereof | |
| US10035802B2 (en) | Solid state forms of ibrutinib | |
| US11149017B2 (en) | Solid state forms of apalutamide | |
| US20210387952A1 (en) | Solid state forms of daprodustat and process for preparation thereof | |
| US8722722B2 (en) | Raltegravir salts and crystalline forms thereof | |
| JP6554617B2 (ja) | １−（５−（２，４−ジフルオロフェニル）−１−（（３−フルオロフェニル）スルホニル）−４−メトキシ−１ｈ−ピロール−３−イル）−ｎ−メチルメタンアミン塩の新規な結晶形 | |
| US8501960B2 (en) | Saxagliptin intermediates, saxagliptin polymorphs, and processes for preparation thereof | |
| US20080033051A1 (en) | Crystal forms of o-desmethylvenlafaxine | |
| US20240368348A1 (en) | Solid state forms of sugammadex sodium | |
| US20090281315A1 (en) | Forms of lapatinib ditosylate and processes for preparation thereof | |
| US20080167477A1 (en) | Novel polymorphic forms of carvedilol dihydrogen phosphate and process for preparing the same | |
| US20180273499A1 (en) | Salts and solid state forms of vortioxetine | |
| US12043597B2 (en) | Crystalline polymorphs of Rivoceranib and Rivoceranib mesylate | |
| US12404267B2 (en) | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl)ethyl]phenyl}-2H-tetrazol-5-yl)-4,5-dimethoxyphenyl]-4-oxo-4H-chromene-2-carboxamide and of its mesylate salt | |
| US11339164B2 (en) | Crystalline form E1 of larotrectinib ethanesulfonate | |
| US20230278990A1 (en) | Solid state forms of n-[2-(2-{4-[2-(6,7-dimethoxy-3,4-dihydro-2(1h)-isoquinolinyl)ethyl]phenyl}-2h-tetrazol-5-yl)-4,5-dimethoxyphenyl]-4-oxo-4h-chromene-2-carboxamide mesylate salt | |
| US11465974B2 (en) | Crystalline polymorphs of Pracinostat and Pracinostat salts | |
| US20200283381A1 (en) | Solid state forms of elafibranor | |
| US20250066327A1 (en) | Solid state forms of danicopan and process thereof | |
| US12391708B2 (en) | Crystalline Lorlatinib : fumaric acid and solid state form thereof | |
| US20090030207A1 (en) | Polymorphs of Dolasetron base and process for preparation thereof | |
| WO2022224269A1 (fr) | Co-cristaux, sels et formes solides de niraparib | |
| US20090062546A1 (en) | Dolasetron trifluoroacetate, polymorphs of dolasetron trifluoroacetate and process for preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: TEVA PHARMACEUTICALS USA, INC., PENNSYLVANIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:TEVA PHARMACEUTICAL INDUSTRIES LTD;REEL/FRAME:020384/0404 Effective date: 20080108 Owner name: TEVA PHARMACEUTICAL INDUSTRIES LTD., ISRAEL Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KOLTAI, TAMAS;PERLMAN, NURIT;NIDAM, TAMAR;AND OTHERS;REEL/FRAME:020383/0100;SIGNING DATES FROM 20071016 TO 20080107 |
|
| AS | Assignment |
Owner name: TEVA PHARMACEUTICALS USA, INC., PENNSYLVANIA Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNMENT OF ASSIGNOR'S INTEREST TO ASSIGNMENT OF RIGHTS IN BARBADOS -- PREVIOUSLY RECORDED ON REEL 020384 FRAME 0404. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF ASSIGNOR'S INTEREST.;ASSIGNOR:TEVA PHARMACEUTICAL INDUSTRIES LTD.;REEL/FRAME:021164/0552 Effective date: 20080108 Owner name: TEVA PHARMACEUTICALS USA, INC., PENNSYLVANIA Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNMENT OF ASSIGNOR'S INTEREST TO ASSIGNMENT OF RIGHTS IN BARBADOS -- PREVIOUSLY RECORDED ON REEL 020384 FRAME 0404;ASSIGNOR:TEVA PHARMACEUTICAL INDUSTRIES LTD.;REEL/FRAME:021164/0552 Effective date: 20080108 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |